Ethanol → HCID 53787920, compound

HRID 1105576Notes

Reaction equation

HRID 1105576 reaction equation
[P:1]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]=O)=[CH:13][CH:12]=1)([S:6][CH2:7][CH2:8][CH3:9])([O:3][CH2:4][CH3:5])=[O:2].C(O)C.[C:22]([NH:30][NH2:31])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(OCC)C>[P:1]([O:10][C:11]1[CH:12]=[CH:13][C:14]([CH:17]=[N:31][NH:30][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:15][CH:16]=1)([S:6][CH2:7][CH2:8][CH3:9])([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 11955BenzoylhydrazineHCID 21442690HCID 21442690, compound

Product 1

HCID 53787920HCID 53787920, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

O-Ethyl S-propyl O-(4-formylphenyl) thiophosphate (5.44 grams; 0.019 mole), ethanol (150 ml) and benzoylhydrazine (2.57 grams; 0.019 mole) were charged into a glass reaction vessel equipped with a mechanical stirrer. The reaction mixture was stirred at room temperature overnight. The reaction mixture was then stripped of ethanol under reduced pressure having a viscous oil as the residue. The residue was then dissolved in diethyl ether resulting in the formation of a precipitate. The ether solution was decanted from the precipitate and was stripped of solvent under vacuum leaving an orange-brown oil. This oil was chromatographed on a silica gel column using methylene chloride and methylene chloride-acetone mixtures as the eluant. Fourteen fractions were recovered and fractions 3 plus 4, 7, 8 and 9 were analyzed by infra red spectroscopy revealing that fraction 8 was the desired product. This fraction was stripped of solvent to yield the desired product O-ethyl S-propyl O-[4-(benzoylhydrazonomethyl)phenyl] thiophosphate as a yellow oil.

Workup

  1. customequipped with a mechanical stirrer
  2. customThe ether solution was decanted from the precipitate
  3. customleaving an orange-brown oil
  4. customThis oil was chromatographed on a silica gel column
  5. customFourteen fractions were recovered

Sources & evidence

ORD record
ord-2cceb835699240f7ab8f3727ab578d0e
Source dataset
uspto-grants-1982_01
Patent number
US04309422

Reaction notes

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